Director of Finance & Billing Operations

RedEye Managed IT Services | New Jersey

RedEye is a New Jersey-based Managed IT Service Provider (MSP) that functions as a fully outsourced IT department for small businesses under 100 employees covering helpdesk, cybersecurity, and strategic technology planning. As we scale our organizational structure, we're building out a dedicated finance and operations function to serve as the backbone of the business.

Position Summary

RedEye is seeking a seasoned Director of Finance & Billing Operations with hands-on MSP industry experience to own the financial and operational engine of the business. This role sits at the intersection of billing, accounting, procurement, vendor management, and account auditing ensuring every dollar we bill, spend, and quote is accurate, efficient, and aligned with our margin targets.

This is not a generic bookkeeping or office admin role. We need someone who has lived inside an MSP's financial systems before — someone who knows ConnectWise Manage and Agreements inside and out, understands how project, labor, and hardware margins work in this industry, and can be a true financial partner to our Account Managers and Service Team.

Key Responsibilities

Billing & Financial Accuracy

  • Own end-to-end billing accuracy across all client agreements, ensuring services delivered match services billed
  • Continually audit client accounts to confirm we're delivering the appropriate level of service relative to what's contracted — flagging scope creep, underbilling, or margin erosion before it becomes lost revenue
  • Reconcile bank and credit card statements
  • Process accounts receivable and client payments
  • Process accounts payable and vendor invoices

 

ConnectWise & Systems Management

  • Serve as the internal expert on ConnectWise Manage and ConnectWise Agreements, ensuring agreements, billing schedules, and service line items are configured correctly
  • Maintain data integrity between ConnectWise and QuickBooks
  • Support KPI reporting tied to project, labor, and hardware margins

Procurement & Vendor Management

  • Manage the full procurement and quoting process for hardware, software, and services
  • Lead vendor negotiations to protect and improve margins
  • Build and maintain vendor relationships that support competitive pricing and reliable fulfillment

Presales & Account Support

  • Partner with Account Managers on presales engineering tasks, including quoting and solution scoping
  • Provide financial and quoting support that helps close deals accurately and profitably
  • Act as a trusted resource to the Service Team on billing and agreement questions

Operations

  • Support broader office operations to ensure the business runs smoothly day to day

Required Qualifications

  • Prior experience working at an MSP (required — this is non-negotiable)
  • Deep, hands-on familiarity with ConnectWise Manage, including ConnectWise Agreements
  • Strong working knowledge of QuickBooks
  • Demonstrated experience with vendor negotiations and procurement
  • Comfort working with and reporting against KPIs tied to project, labor, and hardware margins
  • Experience with quoting processes in a technical services or IT environment
  • Strong attention to detail and a proactive, audit-minded approach to catching billing and margin issues before they become problems
  • Excellent communication skills — able to work cross-functionally with Account Managers, the Service Team, and leadership

Preferred Qualifications

  • Experience managing full-cycle AP/AR
  • Experience reconciling bank and credit card statements
  • Background in a finance, operations, or controller-adjacent role within an MSP or IT services environment

 

 

Why RedEye

This role offers the chance to build and own a critical function inside a growing MSP — with direct visibility into how the business runs financially and real influence over margin performance, vendor relationships, and billing integrity. You'll work closely with leadership and cross-functionally with our sales and service teams, making this a high-impact position for someone who wants ownership, not just a task list.

This is a role with a genuine ability to shape the business, not just maintain it. Our ownership actively encourages and champions people who bring ideas for doing things better — if you see a smarter way to run billing, structure a vendor deal, or tighten up a process, you'll have a real seat at the table to make that case and see it through. We're looking for someone who wants to leave their fingerprint on how this company operates, not just execute a checklist.

Location: hybrid/remote, full remote for the right person

Compensation

Salary range: $65,000–$97,000/yr, based on experience plus bonuses tied to KPI attainment.

Benefits: Health insurance, PTO, 401k + company match, cell phone reimbursement

How to Apply

Please email your resume (PDF format) along with a cover letter to info@redeye.tech

In your cover letter, rather than a generic overview, please address the following directly:

  • Your specific, hands-on experience with ConnectWise Manage and ConnectWise Agreements — what did you do day-to-day?
  • Your experience with QuickBooks and managing AP/AR
  • An example of a vendor negotiation or procurement process you led, and the outcome
  • Of the responsibilities and qualifications listed above, where is your experience strongest, and where is it thinnest?

We're less interested in a broad self-assessment of strengths and weaknesses, and more interested in specifics tied to this role. The goal is to understand exactly what you've done, not how you'd describe yourself in general terms.